Getting Started

I often am asked how I got started dressing to end up where I am today. Let me say that it didn't happen overnight and one day I woke up and said, hmm...I want to wear women's clothes today. It actually started long before I ever put on lipstick or a bra, back to when I was a young child. At the time these incidents meant basically nothing since I was to young to appreciate their true meaning.


The first things that I can remember that I later learned were significant were as follows. When I was about five years old my parents used to have friends over on Friday nights to play cards and socialize. My sister and I used to watch since it was something different to do. All of the women used to wear a lot of makeup, although not like a street walker, it was noticeable none the less. I can remember staring at them with their makeup on and being entranced with them.

At the time of course I didn't know why and a few years later when I was a little older and thought about this I just figured I thought they were pretty and that answered that. Another thing I can remember at about the same time involved of all things, a Looney Tunes cartoon. Everyone about my age remembers them, Bugs Bunny, Elmer Fudd, Foghorn Leghorn, and so on. One particular episode had Elmer Fudd in drag but I can't remember why. He looked just like a woman with all of the makeup, a dress, wig, heels and a womanly figure to boot. I once again found myself strangely attracted to him.

Again I just thought he looked pretty but it stuck in my mind just like my parents female friends with their makeup. There were other things too such as when I was very young I used to be able to push my penis up inside me and I liked it although it was years later until I realized why I liked it. When I hit puberty I still remembered these things and rationalized them as me just thinking they were attractive or hot if you will. By the time I was fourteen I had a girlfriend and led a normal, well adjusted life or so I thought.

When I was about eighteen all this would change when one day when no one was home I was walking through my parents bedroom to look out the front window when on the way back I noticed a tube of lipstick on her dresser. I stopped and looked at it but didn't know why. I picked it up and opened it and was staring at it thinking how pretty it looked.

Then something came over me and since no one was home I looked in the mirror and tried it on. I loved everything about it, not only how it felt and looked but also how it made me feel. I looked at myself for a few minutes before I started to feel guilty and washed it off. In the following days and weeks I was thinking about it, although I was not obsessed, it was a fairly common thought. A short time after that the opportunity presented itself again.

This time in addition to the lipstick I tried some of her blush so I had nice rosy cheeks. I lit a cigarette and started to masturbate while watching in the mirror. This really excited me and it didn't take long before I was finished. Over the next year or so I started to use different kinds of makeup and even found an old wig in the back of a closet. My look was crude because of my inexperience but to me it looked sexy. Back then this was just a sexual thing and I never thought it was anything more, or perhaps that is just what I told myself.

By the time I was in my early twenties I was starting to dress more often and feminine thoughts were running through my mind more often. Then one summer I had a life changing experience that changed me forever. You can read about it in "Summer of Love". At that point dressing and feminine thoughts were making up an increasing part of my life. By the time I reached my early thirties my view on all of this was changing.

I started to become more concerned with looking passable and natural vs sexy or hot. The two are not mutually exclusive as I have found out over the years. As I have gotten older I realized it is not about that I like the way that I look but it's the way I feel inside being brought out to what I see in the mirror. When I realized I was trans gendered (see the story titled the same), everything in my life, including my dressing and femininity made sense.

My look continues to evolve as I do but I like to dress age appropriately so I can go out and blend in as much as possible. I almost forgot to tell you of course my body is shaven and I do my nails and eyebrows. I must be doing something right with the positive comments I receive in chat rooms. I do not consider this "dressing"  since this is the way I'm supposed to look anyway? Thanks for taking a walk down memory lane with me I hope you enjoyed it.